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Macrocyclic inhibitors of hepatitis C virus
8153800 Macrocyclic inhibitors of hepatitis C virus
Patent Drawings:

Inventor: Simmen, et al.
Date Issued: April 10, 2012
Application: 13/197,226
Filed: August 3, 2011
Inventors: Simmen; Kenneth Alan (Tervuren, BE)
De Kock; Herman Augustinus (Arendonk, BE)
Raboisson; Pierre Jean-Marie Bernard (Sterrebeek, BE)
Nilsson; Karl Magnus (Huddinge, SE)
Samuelsson; Bengt Bertril (Huddinge, SE)
Rosenquist; Asa Annica Kristina (Huddinge, SE)
Assignee: Tibotec Pharmaceuticals Ltd. (Eastgate, County Cork, IE)
Primary Examiner: Kifle; Bruck
Assistant Examiner:
Attorney Or Agent: Woodcock Washburn LLP
U.S. Class: 546/154; 548/200; 564/336
Field Of Search: 546/154; 548/200; 564/336
International Class: C07D 215/00; C07D 277/00; C07C 211/00
U.S Patent Documents:
Foreign Patent Documents: 0126587; 0443132; 1090997; 1043399; 1408031; WO 99/07733; WO 99/07734; WO 00/09543; WO 00/09558; WO 00/47561; WO 00/59929; WO 01/74768; WO 02/08198; WO 02/060926; WO 03/035060; WO 03/053349; WO 03/062228; WO 03/062265; WO 03/064416; WO 03/064455; WO 03/064456; WO 03/066103; WO 03/087092; WO 03/099274; WO 03/099316; WO 2004/009121; WO 2004/026896; WO 2004/032827; WO 2004/039833; WO 2004/039970; WO 2004/043339; WO 2004/093915; WO 2004/037855; WO 2004/072243; WO 2004/092161; WO 2004/092203; WO 2004/093798; WO 2004/094452; WO 2004/101602; WO 2004/103996; WO 2004/113365; WO 2005/010029; WO 2005/073195; WO 2005/073216; WO 2007/014918; WO 2007/014919; WO 2007/014920; WO 2007/014921; WO 2007/014922; WO 2007/014923; WO 2007/014924; WO 2007/014925; WO 2007/014927; WO 2007/017144
Other References: US. Appl. No. 11/995,573, filed Jan. 14, 2008, Simmen. cited by other.
U.S. Appl. No. 11/995,714, filed Jan. 15, 2008, Simmen. cited by other.
U.S. Appl. No. 11/995,941, filed Jan. 17, 2008, Simmen. cited by other.
U.S. Appl. No. 10/572,349: Non-Final Rejection dated Nov. 24, 2008, 18 pages. cited by other.
Zanotti et al., "Synthesis of analogues of amaninamide, an amatoxin from the white Amanita virosa mushroom", International Journal of Peptide and Protein Research, 1987, 450-459. cited by other.
Zanotti et al., "Synthesis of Ile3-Amaninamide and its Diastereoisomeric (s)-Sulfoxide from the Analogs of Amanin", International Journal of Peptide and Protein Research, 1981, 162-168. cited by other.









Abstract: Inhibitors of HCV replication of formula (I) ##STR00001## and the N-oxides, salts, and stereoisomers, wherein each dashed line represents an optional double bond; X is N, CH and where X bears a double bond it is C; R.sup.1 is --OR.sup.7 or --NH--SO.sub.2R.sup.8; R.sup.2 is hydrogen, and where X is C or CH, R.sup.2 may also be C.sub.1-6alkyl; R.sup.3 is hydrogen, C.sub.1-6alkyl, C.sub.1-6alkoxyC.sub.1-6alkyl, or C.sub.3-7cycloalkyl; R.sup.4 is aryl or Het; n is 3, 4, 5, or 6; R.sup.5 is halo, C.sub.1-6alkyl, hydroxy, C.sub.1-6alkoxy, phenyl, or Het; R.sup.6 is C.sub.1-6alkoxy or dimethylamino; R.sup.7 is hydrogen; aryl; Het; C.sub.3-7cycloalkyl optionally substituted with C.sub.1-6alkyl; or C.sub.1-6alkyl optionally substituted with C.sub.3-7cycloalkyl, aryl or with Het; R.sup.8 is aryl; Het; C.sub.3-7cycloalkyl optionally substituted with C.sub.1-6alkyl; or C.sub.1-6alkyl optionally substituted with C.sub.3-7cycloalkyl, aryl or with Het; aryl is phenyl optionally substituted with one, two or three substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 to 4 heteroatoms selected from nitrogen, oxygen and sulfur, and being optionally substituted with one, two or three substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.
Claim: What is claimed:

1. A process for the preparation of a compound of formula ##STR00196## comprising the ring closure and dehydration of a compound of formula ##STR00197##

2. The process according to claim 1 wherein the compound of formula (35) is prepared by coupling a compound of formula ##STR00198## with a compound having the formula ##STR00199##

3. The process according to claim 1 wherein the hydroxy function in the compound of formula (36) is converted to a leaving group.

4. The process according to claim 3 wherein the leaving group is a halogen or an arylsulfonyl group.

5. A compound of formula ##STR00200##

6. A compound of formula ##STR00201##

7. A compound of formula ##STR00202##
Description:
 
 
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